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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3g3271

Which statements about the compound shown are correct? Count as alpha hydrogens those on carbons directly bonded to a carbonyl carbon. Select all that apply.

  1. AThe OCH hydrogens of the ethyl group are alpha hydrogens of the ester carbonyl.
  2. BThe CH hydrogens between the two carbonyl groups are the most acidic.
  3. CThere are 5 alpha hydrogens in total.
  4. DIt exists as an equilibrium of keto and enol forms, and the enol is stabilised by conjugation and an intramolecular hydrogen bond.

Answer: B, C, D

The compound shown is ethyl acetoacetate. The alpha hydrogens are the 3 H of the acetyl CH and the 2 H of the central CH, a total of 5; the CH is flanked by two carbonyls and is the most acidic. The OCH carbon is bonded to oxygen, not to the carbonyl carbon, so its hydrogens are not alpha hydrogens. The enol form is stabilised by C=C-C=O conjugation and a six-membered hydrogen-bonded ring.
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